The present invention relates to pyridone derivatives and herbicides containing them as active ingredients.
Heretofore, some 3-(substituted)phenyl-2-pyridone derivatives have been known. However, no more than a few compounds have been known with respect to 3-(substituted)phenyl-6-(substituted)alkyl-2-pyridone derivatives, which represent the characteristic of the compounds of the present invention. For example, the specification of JP-B-46-30190 discloses 3-(4-chlorophenyl)-6-methyl-2-pyridone. Further, U.S. Pat. No. 3,720,768 discloses 3-phenyl-6-ethyl-2-pyridone. However, either specification discloses nothing about herbicidal activities. On the other hand, some 3-(substituted)phenyl-4-pyridone derivatives have been known. However, no more than a few compound have been known with respect to 3-(substituted)phenyl-6-(substituted)alkyl-4-pyridone derivatives, which represent the characteristic of the compounds of the present invention. For example, Chemical Abstract vol. 76, No. 140407, discloses 3-phenyl-6-methyl-4-pyridone, but discloses nothing about the herbicidal activities. Further, the specification of JP-A-62-167708 discloses a 3-(substituted)phenyl-6-(substituted)alkyl-4-pyridone derivative having a carbamoyl group at the 5-position, and a herbicidal activity is also disclosed. However, it is different from the compounds of the present invention.
In recent years, a herbicide is strongly desired which has selective activities to kill only weeds without giving adverse effects to crop plants even when it is applied to the crop plants and weeds simultaneously. Further, it is desired to develop an agent whereby complete effects can be obtained at a low dose, in order to prevent the agent from remaining excessively in the environment.
To solve the above problems, the present inventors have synthesized many pyridone derivatives and conducted various studies on their usefulness. As a result, it has been found that certain pyridone derivatives have excellent herbicidal activities and selectivity to solve the above problems, and the present invention has been accomplished.
Namely, the present invention provides a pyridone derivative represented by the general formula: 
{wherein R is a C1-C6 alkyl group or a C1-C6 haloalkyl group, R1 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, an acetyl group, a group of xe2x80x94Nxe2x95x90CR13R14 or a group of xe2x80x94NR23R24 (provided that when R1 is a hydrogen atom, R is a C1-C6 haloalkyl group), each of R13 and R14 which are independent of each other, is a hydrogen atom, a C1-C6 alkyl group, a group of xe2x80x94NR23R24 or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), each of R23 and R24 which are independent of each other, is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a benzoyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a phenoxycarbonyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a formyl group or a C1-C6 alkylsulfonyl group, R2 is a hydrogen atom, a C1-C6 alkyl group, a carboxyl group or a C1-C6 alkoxycarbonyl group, R19 is a hydrogen atom, a halogen atom, a C1-C6 alkoxy group, a cyano group or a C1-C6 alkyl group, and Q represents a formula of 
[wherein R3 is a hydrogen atom or a halogen atom, R4 is a hydrogen atom, a halogen atom, a nitro group, a C1-C6 alkoxycarbonyl C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl C1-C6 alkylthio group, a C1-C6 alkoxycarbonyl C1-C6 alkylamino group, a benzyloxy group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group or a C1-C6 alkoxy group), a hydroxyl group, a thiol group, an amino group or a cyano group, R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a hydroxyl group, a thiol group, an amino group, a nitro group, a chlorosulfonyl group, an acetylthio group, a cyano group, a cyano C1-C6 alkyl group, a formyl group, a hydroxymethyl group, a group of xe2x80x94YR9, a group of xe2x80x94CR21xe2x95x90NOR9, a group of xe2x80x94CO2R10, a group of xe2x80x94COSR10, a group of xe2x80x94CONR10R11, a group of xe2x80x94SO2NR10R11, a group of xe2x80x94NHCONHR11, a group of xe2x80x94SOR12, a group of xe2x80x94SO2R12, an acyl group, a C1-C6 alkoxy C1-C6 alkyl group, a group of xe2x80x94CO2Nxe2x95x90CR13R14, a group of xe2x80x94CH(OH)R21, a group of xe2x80x94CH2YR9, a hetero ring group or a group of xe2x80x94CH2CH(Cl)CO2R10, Y is an oxygen atom, a sulfur atom or a group of xe2x80x94NR21xe2x80x94, R21 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group or a C3-C6 alkynyl group, R9 is a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C8 cycloalkyl group, a C1-C6 haloalkyl group, a hydroxy C1-C6 alkyl group, a C3-C6 haloalkenyl group, a C3-C8 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a cyano C1-C6 alkyl group, a group of xe2x80x94CH(R15)COYR16, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a group of xe2x80x94CH2 (3-6 membered hetero ring) (the hetero ring group of said group may be substituted by a halogen atom, a nitro group, an oxo group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a 3-6 membered hetero ring group (said group may be substituted by a halogen atom, a nitro group, an oxo group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group) or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), R15 is a hydrogen atom, a C1-C6 alkyl group or a C3-C8 cycloalkyl group, R16 is a hydrogen atom, a c1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C8 cycloalkyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C3-C8 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group) or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxycarbonyl C1-C6 alkyl group or a C1-C6 alkoxy group), R10 is a hydrogen atom, a sodium atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C8 cycloalkyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C3-C8 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 alkoxycarbonyl C1-C6 alkyl group, a C3-C6 alkenyloxycarbonyl C1-C6 alkyl group, a C3-C6 alkynyloxycarbonyl C1-C6 alkyl group, a C3-C8 cycloalkyloxycarbonyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkoxycarbonyl C1-C6 alkyl group, a halo C1-C6 alkoxycarbonyl C1-C6 alkyl group, a halo C3-C6 alkenyloxycarbonyl C1-C6 alkyl group, a benzyloxycarbonyl C1-C6 alkyl group (the benzyl group of said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a C1-C6 alkylthiocarbonyl C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkoxycarbonyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkoxycarbonyl C1-C6 alkyl group, a C1-C6 monoalkylcarbamoyl C6-C6 alkyl group, a C1-C6 dialkylcarbamoyl C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkoxycarbonyl C1-C6 alkyl group, a phenoxycarbonyl C1-C6 alkyl group (the phenyl group of said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), a C1-C6 alkoxycarbonyl C1-C6 alkoxycarbonyl C1-C6 alkyl group, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group) or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group), R11 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C8 cycloalkyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group or a C3-C8 cycloalkyl C1-C6 alkyl group, R12 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C8 cycloalkyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group or a C3-C8 cycloalkyl C1-C6 alkyl group, R6 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkoxycarbonyl C1-C6 alkyl group, a cyano C1-C6 alkyl group, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group or a C1-C6 alkoxy group) or a group of xe2x80x94CH2 (3-6 membered hetero ring), R7 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a cyano group, a C1-C6 hydroxyalkyl group, a group of xe2x80x94CO2R10 a formyl group, an acyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 haloalkylthio C1-C6 alkyl group, a C1-C6 haloalkylsulfinyl C1-C6 alkyl group, a C1-C6 haloalkylsulfonyl C1-C6 alkyl group or a carboxyl group, R8 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, an acyl group, a halogen atom or a nitro group, R20 is a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 haloalkoxy group, a C3-C6 haloalkenyloxy group or a group of xe2x80x94NR11R12, and Yxe2x80x2 is an oxygen atom, a sulfur atom, a group of xe2x80x94NR21xe2x80x94 or a group of xe2x80x94COxe2x80x94]}; and a herbicide containing it as an active ingredient.
In this specification, the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The C1-C6 alkyl group represents a straight chain or branched chain alkyl group having from 1 to 6 carbon atoms. For example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a n-hexyl group, an isohexyl group or a 3,3-dimethylbutyl group may be mentioned.
The C1-C6 haloalkyl group represents a C1-C6 alkyl group substituted by halogen atoms. For example, a difluoromethyl group, a trifluoromethyl group or a pentafluoroethyl group may be mentioned.
The C2-C6 alkenyl group represents a straight chain or branched chain alkenyl group having from 2 to 6 carbon atoms. For example, a vinyl group, a propenyl group, an isopropenyl group, a butenyl group, a pentenyl group or a hexenyl group may be mentioned.
The C3-C6 haloalkenyl group represents a straight chain or branched chain alkenyl group having from 3 to 6 carbon atoms, substituted by a halogen atom. For example, a 2-chloro-2-propenyl group or a 3-chloro-2-propenyl group may be mentioned.
The C3-C6 alkynyl group represents a straight chain or branched chain alkynyl group having from 3 to 6 carbon atoms. For example, a propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a 3,3-dimethyl-1-butynyl group, a 4-methyl-1-pentynyl group or a 3-methyl-1-pentynyl group may be mentioned.
The C3-C8 cycloalkyl group represents a cycloalkyl group having from 3 to 8 carbon atoms. For example, a cyclopropyl group or a cyclohexyl group may be mentioned.
The 3-6 membered hetero ring group may, for example, be a pyrimidinyl group, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, an oxoranyl group, a dioxoranyl group or an oxiranyl group.
Now, specific examples of the compounds of the present invention will be disclosed in Tables 1 to 33. However, the compounds of the present invention are not limited to such compounds. The compound numbers will be referred to in the subsequent description.
(In the Tables, * represents a triple bond, and the same applies hereinafter.)
The compounds of the present invention can be produced, for example, in accordance with the following processes. However, the method for their production is not limited to such processes. 
{In the formulae, R1 is as defined above, X is a halogen atom, Et is an ethyl group, Ac is an acetyl group, and Qxe2x80x2 represents a formula of 
[wherein each of R3, R20, R21 and Y is as defined above, R4xe2x80x2 is a hydrogen atom, a halogen atom or a nitro group, R5xe2x80x2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a nitro group, a group of xe2x80x94YR9xe2x80x2, a group of xe2x80x94SOR9xe2x80x2, a group of xe2x80x94SO2R9xe2x80x2 or a C1-C6 alkoxy C1-C6 alkyl group, R6xe2x80x2 is a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, an oxiranemethyl group or a C1-C6 alkoxy C1-C6 alkyl group, R7xe2x80x2 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a halogen atom or a hydroxyl group, R8xe2x80x2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a nitro group, R9xe2x80x2 is a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 haloalkyl group, a C3-C6 haloalkenyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a benzyloxy group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, C1-C6 alkoxy group, or the like) or a 5-6 membered hetero ring group (said group may be substituted by a halogen atom, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or the like)]}.
By halogenating a compound represented by the general formula (II-1), a compound represented by the general formula (II-2) can be produced. As a halogenating agent, phosphorus tribromide, thionyl bromide, thionyl chloride, hydrogen chloride or hydrogen bromide may, for example, be used. As a solvent, an ether such as diethyl ether, tetrahydrofuran (THF) or dioxane, or a hydrocarbon such as n-hexane, benzene or toluene, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the obtained compound of the general formula (II-2) and a cyaniding agent are reacted to obtain a compound of the general formula (II-3). As the cyaniding agent, sodium cyanide or potassium cyanide may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an alcohol such as methanol or ethanol, or an aprotic polar solvent such as acetonitrile, N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC), may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the obtained compound of the general formula (II-3) is hydrolyzed in the presence of a base or an acid to obtain a compound of the general formula (II-4). As the base, an inorganic base such as sodium hydroxide or potassium hydroxide, may, for example, be used. As a solvent, an alcohol such as methanol or ethanol, or a protic polar solvent such as water, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, in the presence of a condensing agent and magnesium chloride, the compound of the general formula (II-4) and potassium salt of monoethyl malonate are reacted to obtain a compound of the general formula (II-5). As the condensing agent, 1,1xe2x80x2-carbonyldiimidazole (CDI), 2-chloro-1-methylpyridinium iodide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide, diphenylphosphorylazide or triphenylphosphine may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the general formula (II-5) and trifluoroacetonitrile are reacted in the presence of a base to obtain a compound of the general formula (II-6). As the base, an organic amine such as triethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), pyridine, picoline or quinoline, or an inorganic base such as sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As a solvent, an alcohol such as methanol or ethanol, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. Then, the compound of the general formula (II-6) and an orthoformate are reacted in the presence of acetic anhydride to produce a compound of the general formula (II-7). As the orthoformate, methyl orthoformate or ethyl orthoformate may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aprotic polar solvent such as acetonitrile, DMF or DMAC, a carboxylic acid such as acetic acid, or acetic anhydride, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed with from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the general formula (II-7) is hydrolyzed to obtain a compound of the present invention represented by the general formula (II-8). As a base, an inorganic base such as sodium hydroxide or potassium hydroxide, may, for example, be used. As an acid, sulfuric acid or hydrochloric acid may, for example, be used. As a solvent, an alcohol such as methanol or ethanol, or a protic polar solvent such as water, or an ether such as dioxane or THF, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. Further, this compound has keto-enol tautomers.
Then, the compound of the present invention represented by the general formula (II-8) and a compound represented by the general formula (II-9) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (II-10). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the obtained compound of the present invention represented by the general formula (II-10) and a Lewis acid are reacted, and then water is added thereto to obtain a compound of the present invention represented by the general formula (II-11), followed by decarboxylation in the presence of a copper catalyst, to obtain a compound of the present invention represented by the general formula (II). As the Lewis acid, boron tribromide or aluminum trichloride may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an aprotic polar solvent such as acetonitrile, DMF or DMAC, or an alcohol such as methanol or ethanol, may, for example, be used. Further, for the decarboxylation, a high boiling point solvent such as quinoline may be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, as another method, the compound of the present invention represented by the general formula (II-10) is decarboxylated in the presence of dimethylsulfoxide, water and sodium chloride, to obtain a compound of the present invention represented by the general formula (II). The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, Qxe2x80x2, R, R1, R2 and X are as defined above, and R19xe2x80x2 is a hydrogen atom or a C1-C6 alkyl group.)
A compound represented by the general formula (II-3) and a compound represented by the general formula (III-1) are reacted in the presence of a base, followed by treatment with an acid to obtain a mixture comprising a compound of the present invention represented by the general formula (III-2) and a compound represented by the general formula (III-3). As the base, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, or an inorganic base such as sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. As the acid, hydrochloric acid or sulfuric acid may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. Further, the compound of the present invention represented by the general formula (III-2) has keto-enol tautomers.
Then, the obtained compound of the present invention represented by the general formula (III-2) and a compound represented by the general formula (II-9) or 2,4-dinitrophenoxyamine, are reacted in the presence of a base in some cases by using a phase transfer catalyst to obtain a compound of the present invention represented by the general formula (III). As the base, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, or an inorganic base such as sodium, sodium hydride, sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As the phase transfer catalyst, tetra-n-butylammonium bromide or benzyl triethylammonium chloride may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, a carboxylic acid such as acetic acid, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, as another method, the compound represented by the general formula (III-3) and a compound represented by the general formula (III-4) may be reacted to produce the compound of the present invention represented by the general formula (III). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, a carboxylic acid such as acetic acid, an alcohol such as methanol or ethanol, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent under anhydrous condition and is usually completed within from 1 to 24 hours. In some cases, the intermediate amide derivative may be isolated and ring-closed in the presence of an acid catalyst such as p-toluene sulfonic acid. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, the compound of the present invention represented by the general formula (III-2) can be produced also by reacting the compound represented by the general formula (III-6) and a compound represented by the general formula (III-7), as another method. As a solvent, an acid such as acetic acid or polyphosphoric acid, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, the compound represented by the general formula (III-6) can be produced by reacting the compound of the general formula (II-3) and ethyl formate in the presence of a base. As the base, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, or an inorganic base such as sodium, sodium hydride, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an alcohol such as methanol or ethanol, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is completed within a range of from 1 to 24 hours. In some cases, the salt may be isolated, and then acidified with e.g. acetic acid and then withdrawn. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, the compound represented by the general formula (III-3) can be produced by reacting the compound represented by the general formula (III-8) and a compound represented by the general formula (III-1) in the presence of a base, followed by treatment with an acid, as another method. As the base, an organic amine such as lithium diisopropylamide (LDA), triethylamine, DBU, pyridine, picoline or quinoline, or an inorganic base such as sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. As an acid, hydrochloric acid or sulfuric acid may be used. The above reaction is carried out within a range of from xe2x88x9270xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, the compound represented by the general formula (III-8) can be produced by reacting the compound represented by the general formula (II-4) with ethanol in the presence of an acid. As a solvent, ethanol may be used. As the acid, hydrochloric acid or sulfuric acid may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
[In the formulae, each of R3, R4xe2x80x2 and R9 is as defined above, R17 is a C1-C6 alkyl group, and P represents a formula of 
(wherein each of R, R1, R2 and R19xe2x80x2 is as defined above.)]
A compound of the present invention represented by the general formula (IV-1) and a Lewis acid are reacted to obtain a compound of the present invention represented by the general formula (IV-2). As the Lewis acid, boron tribromide or aluminum trichloride may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, a carboxylic acid such as acetic acid, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (IV-2) and a compound represented by the general formula (IV-3), a compound represented by the general formula (IV-4) or diphenyliodonium chloride (when R9 is a phenyl group), are reacted in the presence of a base, or it and a compound represented by the general formula (IV-5) are reacted in the presence of diethyl azodicarboxylate and triphenylphosphine, to obtain a compound of the present invention represented by the general formula (IV). As the base, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, or an inorganic base such as sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogencarbonate or potassium hydrogencarbonate, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, a carboxylic acid such as acetic acid, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3 and R4xe2x80x2 is as defined above, and R18 is a C1-C5 alkyl group or a hydrogen atom.)
A compound of the present invention represented by the general formula (V-1) is subjected to a ring-closure reaction in the presence of cesium fluoride to obtain a compound of the present invention represented by the general formula (V). As a solvent, an N,N-dialkylaniline such as N,N-diethylaniline or N,N-dimethylaniline, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R6xe2x80x2, R17, X and Y is as defined above.)
A compound of the present invention represented by the general formula (VI-1) is subjected to nitration to obtain a compound of the present invention represented by the general formula (VI-2). As the nitration agent, nitric acid or fuming nitric acid, or a mixed acid of nitric acid or fuming nitric acid with sulfuric acid, may, for example, be used. The above reaction is carried out within range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization for column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (VI-2) and a compound represented by the general formula (VI-3) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (VI-4). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, a carboxylic acid such as acetic acid, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (VI-4) is reduced to obtain a compound of the present invention represented by the general formula (VI-5). As the reducing agent, iron or tin/hydrochloric acid, may, for example, be used. As a solvent, a carboxylic acid such as acetic acid, a hydrocarbon such as benzene or toluene, an alcohol such as methanol or ethanol, or water, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (VI-5) and a compound represented by the general formula (VI-6) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (VI). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210 xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2, R9, R11 and X is as defined above.)
A compound of the present invention represented by the general formula (VII-1) is subjected to nitration to obtain a compound of the present invention represented by the general formula (VII-2). As the nitration agent, nitric acid or fuming nitric acid, or a mixed acid of nitric acid or fuming acid with sulfuric acid, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (VII-2) is reduced to obtain a compound of the present invention represented by the general formula (VII-3). As the reducing agent, iron or tin/hydrochloric acid, may, for example, be used. As a solvent, a carboxylic acid such as acetic acid, a hydrocarbon such as benzene or toluene, an alcohol such as methanol or ethanol, or water, may for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (VII-3) and a compound represented by the general formula (IV-3) or (IV-4) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (VII). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. In the case of the reaction with the compound represented by the general formula (IV-4), the formed bis product is hydrolyzed by an aqueous sodium hydroxide solution in ethanol. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, a compound of the present invention represented by the general formula (VII-3) and a compound represented by the general formula (VIII-1) are reacted to obtain a compound of the present invention represented by the general formula (VIII). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2, R9, R10, R11, R12 and X is as defined above.)
A compound of the present invention represented by the general formula (VII-1) and a chiorosulfonation agent are reacted to obtain a compound of the present invention represented by the general formula (IX-1). As the chlorosulfonation agent, chlorosulfonic acid or a mixed solution comprising sulfuric anhydride, sulfuric acid and carbon tetrachloride, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (IX-1) is reduced to obtain a compound of the present invention represented by the general formula (IX-2). As the reducing agent, a mixture of red phosphorus and iodine, or zinc, may, for example, be used. As a solvent, acetic acid may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (IX-2) is subjected to alkali hydrolysis to obtain a compound of the present invention represented by the general formula (IX-3). As a base, sodium hydroxide or potassium hydroxide, may, for example, be used. As a solvent, methanol, ethanol, water or a mixture thereof, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (IX-3) and a compound represented by the general formula (IV-3) or a compound represented by the general formula (IV-4) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (IX). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
In the same manner as above, the compound of the present invention represented by the general formula (IX-3) and a compound represented by the general formula (IV-3xe2x80x2) or a compound represented by the general formula (IV-4xe2x80x2) are reacted in the presence of a base, to obtain a compound of the present invention represented by the general formula (IXxe2x80x2). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (IXxe2x80x2) is oxidized to obtain a compound of the present invention represented by the general formula (IXxe2x80x3) or a compound of the present invention represented by the general formula (IXxe2x80x2xe2x80x3). As the oxidizing agent, hydrogen peroxide, m-chloroperbenzoic acid, sodium hypochlorite or potassium peroxymonosulfate (tradename: Oxone), may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an aprotic polar solvent such as acetonitrile, DMF or DMAC, or a protic polar solvent such as methanol, ethanol or water, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, a compound represented by the general formula (IX-1) and a compound represented by the general formula (X-1) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (X). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R6 and X is as defined above.)
A compound of the present invention represented by the general formula (VI-2) and sodium hydrogensulfide are reacted to obtain a compound of the present invention represented by the general formula (XI-1). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an acid such as acetic acid, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XI-1) is reduced to obtain a compound of the present invention represented by the general formula (XI-2). As the reducing agent, iron or tin/hydrochloric acid, may, for example, be used. As a solvent, a carboxylic acid such as acetic acid, a hydrocarbon such as benzene or toluene, an alcohol such as methanol or ethanol, or water, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XI-2) and CDI are reacted to obtain a compound of the present invention represented by the general formula (XI-3). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210 xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XI-3) and a compound represented by the general formula (VI-6) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XI). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2, R9, R11 and X is as defined above, R22 is a C1-C6 alkyl group, a C2-C6 alkenyl group or a C3-C6 alkynyl group.)
A compound of the present invention represented by the general formula (XII-1) is brominated to obtain a compound of the present invention represented by the general formula (XII-2). As the bromination agent, N-bromosuccinimide (NBS) may, for example, be used. As a catalyst, 2,2xe2x80x2-azobisisobutyronitrile is used, and as a solvent, a halogenated hydrocarbon such as carbon tetrachloride, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII-2) is oxidized to obtain a compound of the present invention represented by the general formula (XII-3). As the oxidizing agent, one prepared from sodium methoxide and 2-nitropropane, may, for example, be used. As a solvent, an alcohol such as methanol or ethanol may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII-3) is treated with hydroxylamine hydrochloride and a dehydration agent to obtain a compound of the present invention represented by the general formula (XII). As the dehydration agent, magnesium sulfate, sodium sulfate or p-toluenesulfonic acid may, for example, be used. Further, they may be used as mixed in some cases. As a solvent, a hydrocarbon such as n-hexane, benzene, toluene or xylene, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII) is hydrolyzed to obtain a compound of the present invention represented by the general formula (XIIIxe2x80x2). As an acid, sulfuric acid or hydrochloric acid may, for example, be used. As a solvent, an alcohol such as methanol or ethanol, or a protonic polar solvent such as water, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XIIIxe2x80x2) and a compound represented by the general formula (XIII-1) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XIII). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII-3) and hydroxyamine hydrochloride are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XIVxe2x80x2). As a base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, a hydrocarbon such as benzene or toluene, or an alcohol such as methanol or ethanol, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XIVxe2x80x2) and a compound represented by the general formula (XIV-1) are reacted in the presence of a base to obtain a compound of the resent invention represented by the general formula (XIV). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Further, as another method, a compound of the present invention represented by the general formula (XII-3) and a compound represented by the general formula (XIV-2) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XIV). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, a hydrocarbon such as benzene or toluene, or an alcohol such as methanol or ethanol, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII-2)) and a compound represented by the general formula (XV-1) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XV). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used, As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example be used. The above reaction is carried out within a range of from xe2x88x9210 xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XII-3) and a compound represented by the general formula (XVI-1) or (XVI-2) are reacted to obtain a compound of the present invention represented by the general formula (XVI-3). As a solvent, an ether such as diethyl ether, THF or dioxane, or a hydrocarbon such as n-hexane, benzene or toluene, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XVI-3) is reacted with dimethylsulfoxide (DMSO) and oxalyl chloride and then oxidized by an addition of a base, to obtain a compound of the present invention represented by the general formula (XVI). As the base, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichioromethane, chloroform or carbon tetrachloride, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9280xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XVI) and a compound of represented by the general formula (XVI-3) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XVIxe2x80x2). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, a hydrocarbon such as benzene or toluene, or an alcohol such as methanol or ethanol, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2 and R10 is as defined above.)
A compound of the present invention represented by the general formula (VII-3) is reacted with tert-butyl nitrite and copper (II) chloride for diazotization and then reacted with a compound represented by the general formula (XVII-1) to obtain a compound of the present invention represented by the general formula (XVII). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2 and R18 is as defined above.)
A compound of the present invention represented by the general formula (XVIII-1) is subjected to a ring-closure reaction in the presence of cesium fluoride to obtain a compound of the present invention represented by the general formal (XVIII). As a solvent, an N,N-dialkylaniline such as N,N-diethylaniline or N,N-dimethylaniline, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of Qxe2x80x2, R13, R14, R23 and R24 is as defined above.)
A compound of the present invention represented by the general formula (XIX-1) is reacted with a compound represented by the general formula (XIX-2) in some cases by means of a Lewis acid to obtain a compound of the present invention represented by the general formula (XIX). As the Lewis acid, p-toluene sulfonic acid or titanium tetrachloride may be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XIX-1) and a compound represented by the general formula (XX-1) are reacted in some cases in the presence of a base to obtain a compound of the present invention represented by the general formula (XX) or a compound of the present invention represented by the general formula (XIXxe2x80x3). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XX) and a compound represented by the general formula (XX-2) are reacted in some cases in the presence of a base to obtain a compound of the present invention represented by the general formula (XXxe2x80x2). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R6 and X is as defined above.)
A compound of the present invention represented by the general formula (XXI-1) is reacted with ammonium thiocyanate to produce the compound of the present invention represented by the general formula (XXI-2). As a solvent, a hydrocarbon such as benzene or toluene, an acid such as acetic acid, or an alcohol such as methanol or ethanol, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXI-2) is reacted with bromine or sulfuryl chloride to obtain a compound of the present invention represented by the general formula (XXI-3). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an acid such as acetic acid, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF and DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXI-3) is diazotized and then hydrolyzed in some cases by means of a catalyst such as copper (II) nitrate or copper (I) oxide, to obtain a compound of the present invention represented by the general formula (XXI). As the diazotization agent, sodium nitrite may, for example, be used, and as a solvent, acetic acid, hydrochloric acid, sulfuric acid, water or a mixture thereof, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIxe2x80x2) and a compound represented by the general formula (XXI-4) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXI). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2 and R18 is as defined above, and R25 is a hydrogen atom or an alkyl group.)
A compound of the present invention represented by the general formula (XXII-1) is brominated to obtain a compound of the present invention represented by the general formula (XXII-2). As the bromination agent, NBS may, for example, be used. As a catalyst, 2,2xe2x80x2-azobisisobutyronitrile may, for example, be used. As a solvent, a halogenated hydrocarbon such as carbon tetrachloride may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXII-2) and a compound represented by the general formula (XXII-3) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXII). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an aprotic polar solvent such as acetonitrile, DMF or DMAC, or an excess amount of the compound represented by the general formula (XXII-3) may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXII) is reacted with boron tribromide to obtain a compound of the present invention represented by the general formula (XXIIxe2x80x2). As the solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9270xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXII-2) and a compound represented by the general formula (XXIII-1) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXIII). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIII) is oxidized to obtain a compound of the present invention represented by the general formula (XXIIIxe2x80x2) or a compound of the present invention represented by the general formula (XXIIIxe2x80x3). As the oxidizing agent, hydrogen peroxide, m-chloroperbenzoic acid, sodium hypochlorite or potassium peroxymonosulfate (tradename: Oxone), may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an aprotic polar solvent such as acetonitrile, DMF or DMAC, or a protic polar solvent such as methanol, ethanol or water, may, for example, be used. The above reaction is carried out within a range of from room temperature to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of P, R3, R4xe2x80x2 and R10 is as defined above.)
A compound of the present invention represented by the general formula (XXIV-1) is brominated to obtain a compound of the present invention represented by the general formula (XXIV-2) or a compound of the present invention represented by the general formula (XXV-1). As the bromination agent, NBS may, for example, be used. As a catalyst, 2,2xe2x80x2-azobisisobutyronitrile may, for example, be used. As a solvent, a halogenated hydrocarbon such as carbon tetrachloride may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
The compound of the present invention represented by the general formula (XXIV-2) is subjected to acid treatment to obtain a compound of the present invention represented by the general formula (XXIV-3). As the acid, sulfuric acid or hydrochloric acid may be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in the presence of a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
The compound of the present invention represented by the general formula (XXIV-3) is oxidized to obtain a compound of the present invention represented by the general formula (XXIVxe2x80x2) As the oxidizing agent, a Jones reagent (CrO3xe2x80x94H2SO4) may be used. As a solvent, a ketone such as acetone may, for example, be used. The above reaction is carried out within a range of from xe2x88x9220xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
The compound of the present invention represented by the general formula (XXIVxe2x80x2) and a compound represented by the general formula (XXIV-4) are reacted in the presence of a catalyst to obtain a compound of the present invention represented by the general formula (XXIV). As the catalyst, sulfuric acid or p-toluene sulfonic acid may, for example, be used. Further, as a solvent, a compound represented by the general formula (XXIV-4) may be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
The compound of the present invention represented by the general formula (XXIVxe2x80x2) is decarboxylated in some cases by means of a catalyst such as copper, to obtain a compound of the present invention represented by the general formula (XXVI). As a solvent, a basic solvent such as quinoline, may, for example, be used, or the reaction can be carried out in the absence of a solvent. The above reaction is carried out within a range of from 100xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
The compound of the present invention represented by the general formula (XXV-1) is reacted with a fluorination agent to obtain a compound of the present invention represented by the general formula (XXV). As the fluorination agent, potassium fluoride may, for example, be used. As a solvent, an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, Qxe2x80x2 is as defined above, and R26 is a C1-C6 alkyl group.)
A compound of the present invention represented by the general formula (II-4) is reacted with thionyl chloride to obtain a compound of the present invention represented by the general formula (XXVII-1). As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. Further, thionyl chloride may be used also as a solvent. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound represented by the general formula (XXVII-1) and a compound represented by the general formula (XXVII-2) are reacted in some cases in the presence of a base to obtain a compound represented by the general formula (XXVII-3). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound represented by the general formula (XXVII-3) is reacted with LDA to obtain a compound represented by the general formula (XXVII-4). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9280xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound represented by the general formula (XXVII-4) is reacted with phosphorus oxychloride to obtain a compound of the present invention represented by the general formula (XXVII) and a compound of the present invention represented by the general formula (XXVIII). As a solvent, diethylaniline, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, may, for example, be used. Further, phosphorus oxychloride may be used as a solvent. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization, column chromatography or liquid column chromatography, as the case requires.
Then, the compound represented by the general formula (XXVII) is reacted with potassium fluoride to obtain a compound of the present invention represented by the general formula (XXVIIxe2x80x2). As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound represented by the general formula (XXVII) is reacted with potassium cyanide to obtain a compound of the present invention represented by the general formula (XXVIIxe2x80x3). As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, or an aprotic polar solvent such as acetonitrile, DMF, DMAC or DMSO, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXVII-4) and a compound represented by the general formula (XXVII-5) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXVIIIxe2x80x2) and a compound of the present invention represented by the general formula (XXVIIxe2x80x2xe2x80x3). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, may, for example, be used. As a solvent, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF, DMAC or DMSO, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 48 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization, column chromatography or liquid column chromatography, as the case requires. 
(In the formulae, each of P, R3, R6, R17, R21 and X is as defined above.)
A compound of the present invention represented by the general formula (XXIX-1) is reacted with boron tribromide to obtain a compound Qf the present invention represented by the general formula (XXIX-2). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9270xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIX-2) and a compound represented by the general formula (XXIX-3) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXIX-4). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIX-4) is reacted with a reducing agent to obtain a compound of the present invention represented by the general formula (XXIXxe2x80x2). As the reducing agent, iron powder or tin, may, for example, be used, and in some cases, hydrochloric acid is used. As a solvent, a hydrocarbon such as benzene or toluene, an ester such as ethyl acetate or methyl acetate, an acid such as acetic acid, an alcohol such as methanol or ethanol or water, may, for example, be used. Further, in some cases, these solvents may be used as mixed. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIXxe2x80x2) and a compound represented by the general formula (XXIX-5)) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXIX). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXIX-2) is reacted with a reducing agent to obtain a compound of the present invention represented by the general formula (XXX-1). As the reducing agent, iron powder or tin, may, for example, be used, and in some cases, hydrochloric acid may be used. As a solvent, a hydrocarbon such as benzene or toluene, an ester such as ethyl acetate or methyl acetate, an acid such as acetic acid, an alcohol such as methanol or ethanol, or water, may, for example, be used. Further, in some cases, these solvents may be mixed for use. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXX-1) is reacted with CDI to obtain a compound of the present invention represented by the general formula (XXXxe2x80x2). As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, an alcohol such as methanol or ethanol, or an aprotic polar solvent such as acetonitrile, DMF or DMAC, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.
Then, the compound of the present invention represented by the general formula (XXXxe2x80x2) and a compound represented by the general formula (XXX-2) are reacted in the presence of a base to obtain a compound of the present invention represented by the general formula (XXX). As the base, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, THF or dioxane, a hydrocarbon such as n-hexane, benzene or toluene, an aliphatic ketone such as acetone or methyl ethyl ketone, or an aprotic polar solvent such as acetonitrile, DMF, DMAC may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires. 
(In the formulae, each of R3 and R4xe2x80x2 is as defined above, and R5xe2x80x2 is a C1-C6 alkoxy group, a C3-C6 alkynyloxy group, a C3-C6 alkenyloxy group or a C1-C6 alkyl group.)
A compound represented by the general formula (XXXI-1) and methoxymethyl chloride are reacted in the presence of a Lewis acid to obtain a compound of the present invention represented by the general formula (XXXI). As the Lewis acid, titanium tetrachloride or aluminum chloride may, for example, be used. As a solvent, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, or an ether such as diethyl ether, THF or dioxane, may, for example, be used. The above reaction is carried out within a range of from xe2x88x9210xc2x0 C. to the boiling point of the solvent in some cases in a nitrogen stream and is usually completed within from 1 to 24 hours. The object compound can be isolated from the reaction solution by a conventional method. Further, it is purified by recrystallization or column chromatography, as the case requires.